Shadyside Under Canopy of Tree and Mansion

Some of the greatest times of my pre-traveling life were spent drinking Yuenglings with a crowd of friends on the front porch of the Harris Grill.

I met a guy back then, we’ll call him Willy, who was simultaneously a pot salesman and a neuroscientist. He knew everyone in Pittsburgh, or so it really did seem, and introduced me to them all. I considered him one of my two closest friends at the time. Along with a strictly platonic and strictly kick ass party girl who we’ll call Mary Price, we hung out three to five nights a week with a variety of random whoever was available. The front porch of the Harris Grill became our de facto meetup, to the point where we barely even needed to communicate the likely hood of meeting up there on any given Tuesday, Thursday, Friday or Sunday. We’d start as one table, knowing about all of the staff from various after-parties at Willy’s house, and would over the course of the night end up pulling up another, then another of their black metal tables, the best outdoor seating in Pittsburgh, until we were, essentially, 90% of the bar’s crowd that night.

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I came to know one of the owners, an intimidatingly large bald man who had the smile of an imaginary childhood best friend and the heart to go with it, and rarely a night spent there would go by without him buying me a beverage or at the very least, sitting down with us for a friendly “so what’s the new news since two days ago?” I eventually made my own shirt that read “I heart Harris” and on the back, read “Thursday is Nathan Night”, a testament to the staff’s shirts which read “Tuesday is Bacon Night”, due to the idiosyncrasy the bar held where baskets of bacon were given away for free—or maybe $1, I can’t recall precisely, having been a vegetarian at the time—on that particular night of the week. It’s just that great of a place, you want to become a part of it all.

But to call Harris Grill a “bar” is not entirely correct. The food is killer, the menu is even better, written by a different owner, it’s worth stopping in just to read through the descriptions of the appetizers and entrees which packs more laughs in per line than a second viewing of the original British The Office. They’d set a fire pit out in the winter months, for us smokers after Pittsburgh banned smoking in most establishments, and we’d wear gloves and revel in our love for a city coming up. Before I knew many people at this fine establishment, I’d play Word Dojo with strangers on the Megatouch in the corner of the thick wooden bar, taps sporting craft beers before I could appreciate anything much more potent than the taste of Miller Light. Harris was actually the first place I was introduced to craft beers. I drank my first IPA in those hallowed halls and, though I wasn’t appreciative at the time, shall never forget the introduction.

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But for all its merits, perhaps the most beautiful thing about Harris Grill is the location. Situated just about directly mid-way on Pittsburgh’s self-proclaimed “gayest street”, Ellsworth Avenue, it provides immediate access to a rue completed by a coffee shop, pizza, a dive bar that welcomes smoking, a couple of too-upscale-for-my-tastes nightclubs, vintage and boutique shops, and an ambience that can only be described as utterly metropolitan. The sound of freight trains passing through, dividing the neighborhood from a Whole Foods just across the tracks, mingles with the clink of rich women’s bracelets and brilliant Asian kids commuting to nearby CMU—one of Pittsburgh’s universities where America’s future builds things like sentient robots.

If Ellsworth is the headquarters of all things fabulously chic about Pittsburgh, nearby Walnut Street is the bygone era turned corporate. Once a home to hippies wielding dingy guitars and talking about the pot revolution, it’s now a bastion for the GAP, Banana Republic and American Apparel. Not without its pricey jewelry, art and less-local Pottery Barn stores, it’s still a destination for hipsters and the high class alike. I particularly recommend Crapes Parisienne, the only place in all of my travels to date where I’ve had a savory crepe that makes me wish I had ordered two. The line will be long, the portions will be ample, the seating will be sparse, and the experience will be all too well worth it.

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Aside from binge drinking, gluttony and participating in mass consumerism, though, Shadyside is an ideal place for an activity that requires absolutely no money. Walking the tree-lined canopied streets you’ll be traversing via foot the history of Pittsburgh’s fattest cats. Where steel workers built this city, their upper management associates built massive houses in this neighborhood, beautiful Victorian structures often now covered in Ivy or too big to own in today’s market and therefore abandoned stone castles live between apartment complexes and a Korean Church welcoming gays and lesbians any day, any time. One of my favorite activities while living here was, on all too common rainy days in the Steel City’s Shadyside neighborhood, popping an umbrella over my head and walking the mostly deserted-while-downpouring streets, having the views and each block of sidewalk all to myself, my own thoughts swirling between the wet and the weird this neighborhood has to offer.

Published: October 12, 2012Updated: October 27, 2016

Nathan is the Editor-in-Chief around these parts, and has been traveling by train, bike, VW Bus and Airstream since 2008. He's on Instagram.